Enterprise networks often include a large number of networking devices such as routers, switches, servers, and the like. During the lifespan of a networking device, the manufacturer of the device may issue any number of software updates/upgrades, to fix bugs, address security concerns, and/or provide new features to the device. However, despite the various benefits of installing updates to the devices in a network, many network administrators choose to delay installing an update or opt against performing an update entirely. For example, some administrators may only upgrade the devices in a network every two years, to install the cumulative updates that were released since the last time the devices were updated.